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Synlett 2020; 31(13): 1295-1297
DOI: 10.1055/s-0040-1707852
DOI: 10.1055/s-0040-1707852
letter
Potassium Carbonate Promoted Nucleophilic Addition of Alkenes with Phosphites
We thank the National Natural Science Foundation of China (21861024, 21571094, 21571094) for financial support.
Further Information
Publication History
Received: 12 December 2019
Accepted after revision: 08 May 2020
Publication Date:
18 June 2020 (online)
◊ These authors contributed equally to this work.
Abstract
A facile hydrophosphonylation of alkenes by phosphites promoted by potassium carbonate was developed. The reaction features include easy handling, environmental friendliness, and avoidance of the use of strong bases. A variety of alkenes are tolerated in this reaction, with moderate to excellent yields.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707852.
- Supporting Information
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- 15 Butyl 3-(Diphenylphosphoryl)propanoate (3a); Typical Procedure A mixture of 1a (0.4 mmol), 2a (0.8 mmol), and K2CO3 (0.8 mmol) in DCE (2 mL) was heated at 100 °C under N2 for 4 h. The mixture was then extracted with DCE (3 × 5 mL) and the combined organic phase was dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by TLC [silica gel, PE–EtOAc (3:1)] to give a colorless liquid; yield: 132 mg (95%). 1H NMR (400 MHz, CDCl3): δ = 7.68 (dd, J = 10.9, 7.6 Hz, 4 H), 7.43 (dd, J = 21.7, 6.4 Hz, 6 H), 3.96 (t, J = 6.6 Hz, 2 H), 2.55 (s, 4 H), 1.48 (pent, J = 6.8 Hz, 2 H), 1.25 (hept, J = 7.3 Hz, 2 H), 0.82 (t, J = 7.4 Hz, 3 H). HRMS (ESI): m/z [M + H]+ calcd for C19H24O3P: 331.1458; found: 331.1467.